[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([F:13])[F:12].[H-].[Na+].[CH3:16][Si:17]([CH2:20][CH2:21][O:22][CH2:23]Cl)([CH3:19])[CH3:18].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:23][O:22][CH2:21][CH2:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[C:6](=[O:11])[C:5]2([F:13])[F:12]To a solution of 5-bromo-3,3-difluoroindolin-2-one (600 mg, 2.42 mmol) in DMF (5 mL), 60% NaH (69.6 mg, 2.90 mmol) was added. The resulting mixture was stirred at rt for 20 min and SEM-Cl (472 μL, 2.66 mmol) was added. The reaction mixture was stirred at rt overnight, poured into saturated NH4Cl (40 mL) and extracted with DCM (3×20 mL). The combined DCM layers were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0-100% EtOAc/hexanes) to obtain 5-bromo-3,3-difluoro-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one, which was subjected to borylation using the methods described in Example 32, Step B to obtain compound 37a. 1H-NMR (CDCl3, 400 MHz) δ (ppm): 8.33 (s, 1H), 8.04 (d, J=9.6 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 5.46 (s, 2H), 3.75 (m, 2H), 1.27 (s, 12H), 0.95 (m, 2H).
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